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43 Photos
RED HORSE REAL ESTATE
$625,000
3 BD | 4 BA
Residential - Single Family

Stunning contemporary high-tech home. Custom built. Ideal for entertaining and large gathering. The spacious living room flows into an open dining and large kitchen with stainless & granite. Primary bedroom and full bath along with a 2nd bedroom and full bath plus laundry are all on the first floor. 3rd bedroom and full bath are in the loft and 2 extra rooms; full bath and a huge family room are downstairs. This also would be a perfect Air B & B. Charging station, fiber optics. Beautiful creamy wood floors and vaulted high ceilings, custom shaped windows throughout the house bring in beautiful day light. Two Ponds for kayaking & swimming are walking distance. Central A/C, propane heat. Circular driveway, Southern exposure. Roof solar system owned. MUST SEE.


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$630,000
4 BD | 3 BA
Residential - Single Family

A Berkshire landmark ready for its next chapter. Once home to the beloved BONDHU and Mill on the Floss restaurants, this multi-use property offers endless opportunity -- from a charming single-family residence to a live/work haven, a boutique inn, or a luxury destination dining experience reborn. The second-floor living quarters feature four bedrooms, including a primary suite, plus an open living and dining area. A chef's kitchen with granite countertops and high-end stainless steel appliances completes the space. Perfectly situated along the scenic Route 7 corridor between Williamstown and Pittsfield, this one-of-a-kind property invites vision and imagination to bring it to life once again. Call today for a private tour!


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LANCE VERMEULEN RE, INC
$630,000
4 BD | 3 BA
Residential - Single Family

Fantastic 4 BR Otis Wood Lands Contemporary situated at the end of a cul-de-sac close to all community amenities! This spacious home has great spaces for family and friends. Price includes furniture. Community amenities include pool, tennis/pickleball courts, fitness room, playground, lodge, lake and beach. New septic in 2023, new hot water heater 06/2025, new roof 2003. $4,000 reserve fund fee due from buyer at closing.


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JIMINY REALTY
$689,000
3 BD | 3 BA
Residential - Condo/Townhouse

Step into this beautifully updated 3-bedroom, 3-bathroom retreat nestled in one of Jiminy's most family-friendly neighborhoods. 2 bedrooms and 2 Full baths on the 1st floor. The open-concept living area features floor-to-ceiling windows that flood the space with natural light, highlighting the elegant hardwood flooring and cozy fireplace. The gourmet kitchen boasts quartz countertops and top-of-the-line stainless steel appliances, perfect for entertaining. The primary suite offers a spa-inspired bathroom with a walk-in shower. Outside, the meticulously landscaped, fenced-in patio provides a private sanctuary, complete with plenty of room for al fresco dining. Enjoy the convenience of being just a short walk from the slopes and local shops. This captivating property won't last long.


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WILLIAM PITT SOTHEBY'S - LENOX
$699,000
3 BD | 2 BA
Residential - Single Family

Discover your dream retreat in this stunning log home, nestled on 37 acres of breathtaking land that adjoins over 1,000 acres of serene state forest. This oasis offers an unmatched blend of tranquility and natural beauty, allowing you to escape from the hustle and bustle of everyday life. Imagine sipping your morning coffee on the wrap-around deck, soaking in the picturesque mountain views. Indulge in the ultimate relaxation experience with a soak in your wood-fired hot tub or a rejuvenating session in your outdoor sauna. Step inside and be captivated by the charming open floor plan. The chef's kitchen is a culinary enthusiast's dream, featuring a large island, elegant granite countertops, and a high-end Viking stove, perfect for entertaining guests or creating culinary masterpieces.


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CLARK REALTY GROUP LLC
$699,900
4 BD | 5 BA
Residential - Single Family

Beautiful 4 bedroom contemporary on Lilybrook Road. Vaulted entry way leads to living (sitting) room flanked by formal dining room. Also on the first floor is oversized great (family) room with fireplace, large eat-in kitchen and private master (in-law) suite with full bath and jet tub. The second floor has another master suite with full private bath, two additional bedrooms, and a second full bath. This is perfect for a multi generational family. The basement has plenty of storage and a dry, carpeted rec room with a wet bar and a half bath. The grounds feature mature landscaping and privacy. The roof, skylights, and gas fireplace are newer (installed in 2016). Home is on a private street with a cul-de-sac and is within walking distance to BCC and the state forest. Bosquet and Jiminy Pe


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COHEN & WHITE ASSOCIATES
$730,000
5 BD | 5 BA
Residential - Condo/Townhouse

Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and serenity.Second level has ample space with three guest bedrooms, two full baths and loft/office space open to the great room.The lower level walkout family room is gracious in size and has direct access to your private stone patio. Additionally, you have the fifth bedroom, full bath, laundry room and bonus storage room.Enjoy the association pool, Bousquet Mountain next door and all of the


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THE KINDERHOOK GROUP - PITTSFIELD
$750,000
4 BD | 4 BA
Residential - Condo/Townhouse

Beautifully redone unit at desirable South Pond. Great views from all windows. Freshly remodeled kitchen and baths. Many association amenities like pool, Richmond Pond access and tennis.


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COHEN & WHITE ASSOCIATES
$759,000
3 BD | 3 BA
Residential - Condo/Townhouse

Thoughtfully updated end unit located at the Pines at Bousquet The first level includes a gracious entry with custom flooring and cedar hall closet that flows beautifully into the great room with vaulted ceilings, gas fireplace and glass doors to the screened porch and deck with a scenic view of the woods. The lovely updated kitchen is open to the dining area and great room for comfortable open common spaces. The primary bedroom has wood flooring, walk-in fitted closet and tastefully renovated en-suite bath with custom finishes. Included on the main level is the charming half bath, garage with storage and laundry room. The second floor features a large loft flex space with oversized closet, two guest bedrooms and stunning full bath. The lower level walkout is


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MACCARO REAL ESTATE
$760,000
4 BD | 3 BA
Residential - Single Family

Renovated beautifully in 2023, this contemporary home is on 3.31 acres , includes a .22-acre parcel on Lake Garfield. Built in 1987 this four bedroom, 3 bath contemporary home is nestled in a wooded grove approximately 1/2 mile from the public beach at Lake Garfield. Enter the light filled living area with 1/2 cathedral ceiling and fireplace. There is an efficient kitchen layout with access to a charming, screened porch and an incredibly spacious deck. Two bedrooms and a full bath complete this main floor. The second floor consists of two spacious bedrooms each with its own bath. The primary bedroom has a large walk-in closet and a Juliet balcony overlooking the backyard. Please read the Supplemental Remarks to learn more about the house & lake lo


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LANCE VERMEULEN RE, INC
$775,000
3 BD | 2 BA
Residential - Single Family

Beautifully Built New Construction in SheffieldMove-in ready and thoughtfully crafted by a local custom builder, this 3-bedroom, 2-bath home sits on 1.64 private acres. The open-concept living, dining, and kitchen area flows seamlessly to a lovely backyard patio--perfect for indoor-outdoor living. Nearby hiking, biking, and skiing offer endless recreation, or simply relax and enjoy the peaceful surroundings. Conveniently located just minutes from Sheffield village, Canaan (CT), and Great Barrington, this versatile property works beautifully as a full-time residence, vacation retreat, or investment opportunity in the heart of the Berkshires. This is a new build, and taxes have not yet been determined.


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COHEN & WHITE ASSOCIATES
$789,000
2 BD | 3 BA
Residential - Condo/Townhouse

This White Pines Garden Unit is a must see if you are considering condominium living in this sought after community. Open living Great Room/kitchen/dining with double volume glass to take in the view, fireplace & guest bath on main level. The lower level greets you with a tiled floor sunroom w/direct access to the spacious decking w/private courtyard outdoor space. The primary ensuite, guest bedroom w/full bath & laundry & office/flex space complete this level. This unit boasts a most convenient covered carport space. Assoc. amenities include a clubhouse w/exercise rm, indoor heated pool, 2 Har Tru tennis courts, hiking and walking trails, private beachfront on the Stockbridge Bowl with swimming and kayak & canoe storage or anchor your boat... ..all this and only minutes to Tanglewood


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WILLIAM PITT SOTHEBY'S - LENOX
$814,900
4 BD | 3 BA
Residential - Single Family

Escape to an exceptional Post & Beam Berkshire Retreat nestled on the east side of Jiminy Peak Mountain Resort. Set on 25+ acres for seclusion and privacy, eat, play & live in this 4 bedroom, 2.5 bath chalet-style home with countless modern updates. Spectrum was recently added for everyday internet and tv streaming, as well as 5 new high-efficiency mini split air conditioning/heating units for those steamy Summer, and cold Winter, nights. New granite countertops and GE Cafe and Bosch stainless appliances in the recently refurbished kitchen are a true cook's delight. An open living concept, under a soaring 25 foot ceiling, creates multiple gathering spaces from the huge sectional to the plentiful island seating, and floor to ceiling dining room window frames the outdoors inside.


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WILLIAM PITT SOTHEBY'S - LENOX
$875,000
3 BD | 2 BA
Residential - Single Family

Welcome to this exceptional 3-bedroom, 2-bathroom lakefront retreat w/an in-ground pool,located in the highly sought-after Otis Woodlands community. Perfectly situated on OWL Lake, this home offers a rare combination of natural beauty, modern upgrades, and an array of resort-style amenities, making it the ideal country escape or full-time residence.Step inside to an open-concept living area with soaring vaulted ceilings and abundant natural light streaming through large windows. The spacious kitchen boasts gleaming granite countertops, newer appliances, and custom cabinetry, creating the perfect space for entertaining or quiet meals. The living room, with its inviting warmth and charm, seamlessly flows into the dining area, making this home perfect for gatherings with family and friends.


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COHEN & WHITE ASSOCIATES
$875,000
3 BD | 3 BA
Residential - Single Family

Discover the perfect blend of comfort and charm with this stunning contemporary situated on two acres. There is a full-house Generac generator for comfort and peace of mind and central air. The great room is washed with natural light from the wall of windows and has a beautiful gas fireplace to provide additional warmth on cold Winter days. There is a circular flow into the spacious dining room and the updated kitchen making this home ideal for entertaining. A full bath and two charming guest bedrooms welcome visitors and offer opportunities for a home office. The oversized four-season sunroom offers magnificent light that takes in the picturesque landscaped surroundings and woodlands. It features an efficient gas stove for chillier days and screen inserts to help capture Summer breezes.


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WILLIAM PITT SOTHEBY'S - LENOX
$889,900
5 BD | 4 BA
Residential - Single Family

Pride of ownership reasonates through this disctinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut St. near the esteemed Pittsfield Country Club, BUpstreet Cultural District and is ideally just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character boasting five bedrooms, two and half baths thoughtfully improved over this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring guest house featuring 3 bedrooms, 1 bath plus a first floor in-law bedroom suite and a 2 car garage, if one so chooses to accommodate extended family, friends or caregiver


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COHEN & WHITE ASSOCIATES
$895,000
3 BD | 4 BA
Residential - Single Family

PANORAMIC VIEW, PRIVACY AND A STUNNING CONTEMPORARY is waiting to become your country sanctuary. As you drive up the long, private driveway, you feel your shoulders relax and then..peaceful thoughts take over as you soak in the sweeping south west view at the top of your private hill. The multi-level design of this home offers living with peace and tranquility for both gathering and quiet time alone, all while capturing the nature surrounding you on 5+ acres. Main level bedroom with private deck, full bath, office, cozy den and open kitchen/dining with direct access to the attached 3 car heated garage for convenience, dramatically opens to the Great Room in one direction and the primary bedroom with fireplace and newly designed luxurious ensuite bath with another guest bedroom and bath on


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LANCE VERMEULEN RE, INC
$935,000
4 BD | 3 BA
Residential - Single Family

This is the one you've been waiting for. A classic mid-century home on over 4 private acres, offering the ultimate Berkshire lifestyle. The bright, open-mid century floor plan provides a seamless flow, while two fireplaces add classic comfort. The home features 4 bedrooms, 3 baths, large office and a media room, offering flexibility for family and guests. Outside, your private resort awaits. A beautiful heated swimming pool and a dedicated tennis court provide endless recreation. The expansive grounds, located at the end of a quiet road, guarantee unmatched privacy. Plus, a large solar array and new heating system drastically cuts utility costs. Enjoy total seclusion while being in the middle of everything that makes Great Barrington one of the most desirable towns in the Berkshires.


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KELLER WILLIAMS REALTY
$995,000
3 BD | 3 BA
Residential - Single Family

Nestled in the heart of the Berkshires, 257 W Mountain Road offers a rare blend of luxury and tranquility. This exquisite property is set on a serene, tree-lined road just minutes from downtown Lenox and Tanglewood. With refined finishes, spacious living areas, and walls of windows framing the lush landscape, every detail reflects elegance and comfort. The landscaped grounds feature stone patios, rolling lawns, and wooded privacy--an idyllic retreat for all seasons. Perfect for entertaining or peaceful living, this is Berkshire living at its finest.


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$998,000
4 BD | 4 BA
Residential - Single Family

Berkshires Sanctuary - A Fully Renovated Retreat with Appalachian Trail Access & Nearby Three Mile Pond.Tucked away in a landscape of towering trees and rolling hills, this exquisite four-bedroom and three-bathroom, retreat has been reimagined with over $650,000 in premium renovations, offering the perfect balance of luxury and nature. With direct access to Appalachian trail and Three Mile Pond, just minutes away, this home is a haven for those who crave both serenity and adventure.Where Modern Elegance Meets Natural Beauty A Grand Welcome - A wraparound deck, inground pool, and upper balcony invite you to take in the forested surroundings, framed by black aluminum railings and Trex boards built for beauty and longevity.

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